Preparation method and application of double-photon fluorine ion fluorescent probe compound

A technique for fluorescent probes and compounds, applied in the field of fluorescent probes, can solve the problems of inability to quantitatively measure fluoride ion content, the probe does not report a working curve, and autofluorescence will interfere, achieving good sensitivity and selectivity, and good promotion. Prospect, good water solubility effect

Inactive Publication Date: 2016-07-20
UNIV OF JINAN
View PDF4 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, CN104449677A provides a preparation method and application of a fluoride ion fluorescent probe based on benzothiazole, which can be applied to the detection of fluoride ions in cells, but it has the following disadvantages: 1. The probe is a quenching fluorescent probe, which is not conducive to the observation of biological imaging; 2. The excitation wavelength of the probe is 300nm, which has a certain harmful effect on organisms, and the a...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method and application of double-photon fluorine ion fluorescent probe compound
  • Preparation method and application of double-photon fluorine ion fluorescent probe compound
  • Preparation method and application of double-photon fluorine ion fluorescent probe compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1, the synthesis of probe molecule compound I

[0038] (a) Take 1.106g of 2,4-dihydroxybenzaldehyde and 0.816g of imidazole in a three-necked flask under nitrogen protection. Take 1.3mL of cyclohexenone and add it into the flask; add 6mL of tetrahydrofuran and 6mL of water into the flask. React at ℃ for 72h, then add 20mL of 1M dilute hydrochloric acid, extract the aqueous phase with ethyl acetate, evaporate the solvent, use the mixture of ethyl acetate and n-hexane with a volume ratio of 1:6 as the developing solvent, and separate by column chromatography to obtain 0.46 g compound II, yield 19%;

[0039] (b) Dissolve 0.1g of compound II, 0.331g of tert-butyldimethylchlorosilane, and 0.163g of imidazole in 10mL of dichloromethane, react for 8 hours at room temperature under nitrogen atmosphere, distill off the solvent, and use a volume ratio of 10:1 A mixed solvent of petroleum ether and ethyl acetate was used as a developer and separated by column chromatog...

Embodiment 2

[0040] Embodiment 2, fluorescence experiment

[0041] Take the fluorescent probe compound prepared in Example 1, dissolve it in an aqueous solution containing 5% ethanol, adjust the pH=7.4 with HEPES buffer solution; obtain the fluorescent probe solution, and set aside;

[0042] 1. Take the fluorescent probe solution and divide it into 11 groups, 10mL in each group. Among them, 1 group does not add anion, and 10 groups add CO 3 2? , SO 4 2? , NO 3 ? , Cl ? , I ? 、Br ? 、CH 3 COO ? , N 3 ? 、PO 4 3? , F ?solution, so that the concentration of the probe compound contained in each group of solutions is 10 μM, and the anion concentration is 300 μM, so that the molar ratio of the anion to the probe compound is 30:1; the excitation wavelength is 422 nm, and the fluorescence intensity is tested by a fluorescence photometer. The invention probe solution itself has no fluorescence. Once fluoride ions are added, the fluorescence of the solution at 511nm increases rapidly, b...

Embodiment 3

[0044] Embodiment 3, cell imaging experiment

[0045] MCF-7 cells were cultured in 1 mL cell culture medium containing 10% bovine fetal serum for 12 hours, then treated with 100 μM fluoride ion for 10 minutes, and then treated with 10 μM fluorescent probe of the present invention for 30 minutes. Cells were excited with a light source with an excitation wavelength of 534 nm and imaged under a confocal microscope. Such as image 3 A picture of MCF-7 cells cultured with the addition of fluoride ions for the fluorescent probe of the present invention.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a preparation method and application of a double-photon fluorine ion fluorescent probe compound. The formula of the double-photon fluorine ion fluorescent probe compound is as shown in formula I. The preparation method includes: allowing 2, 4-dihydroxy benzaldehyde and cyclohexenone to react under nitrogen protection by using imidazole as the catalyst; allowing the product obtained by separation to react with tert-butyldimethylsilyl chloride to obtain the pure fluorine ion fluorescent probe compound. The fluorine ion fluorescent probe compound has the advantages that the probe compound has good selectivity and sensitivity to fluorine ions and is nontoxic to cells; probe molecules can be stimulated by double photons to avoid an ultraviolet region, so that the probe molecules are applicable to detection of the fluorine ions in water and detection and imaging of the fluorine ions in cells.

Description

technical field [0001] The invention relates to a fluoride ion fluorescent probe compound and its preparation and application, belonging to the technical field of fluorescent probes. technical background [0002] Fluorine is a non-metallic element and an essential trace element for the human body. A small amount of fluorine can replace phosphorus to build teeth and make them stronger. Drinking water and toothpaste contain appropriate amounts of fluoride ions that can effectively prevent dental caries. Too much fluorine in the human body Too much fluoride can lead to dental fluorosis and bone disease, and too little fluoride in the human body can lead to osteoporosis and dental caries. Therefore, the qualitative and quantitative detection of fluoride ion is of great significance. [0003] Due to its advantages of high sensitivity, good selectivity, and fast response, fluorescent probe detection has attracted the attention of researchers in recent years. The excitation wavel...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07F7/18C09K11/06G01N21/64
CPCC07F7/1804C07F7/188C09K11/06C09K2211/1088G01N21/6428G01N21/6486
Inventor 吕正亮史孝民范春华
Owner UNIV OF JINAN
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap